Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite

Bungalow in Richmond

4.99 out of 5 average rating, 217 reviews

Artist's Retreat Guest House

The Artist's Retreat Guest House is a two-bedroom Craftsman bungalow in the Earlham College neighborhood that welcomes adults visiting our community of Richmond, Indiana. Fast Wifi and cable provided. It features a warm, spacious living area, a fully equipped kitchen, a library filled with art books, an artist's studio, a garden, fine antiques, and representative works by artists of both regional and international note. Many art pieces are fragile or heavy, so no children, pets, or smoking.

Oct 20 – 27

G$27,815 GYD per night

Guest favorite

Guest suite in Muncie

4.97 out of 5 average rating, 219 reviews

The Eagles Nest, two bedroom retreat.

Peaceful, centrally-located historic 1892 Queen Anne Victorian home. The Eagle's Nest has private entrance, off street parking, 2 bedrooms, furnished suite on the 2nd floor overlooking White River. Walk 0.6 miles to downtown Muncie, less than 2 miles to Ball State Univ. and 2 blocks to the Bob Ross Experience (Minnetrista). Nearby eatery and brewery options. Just 29 steps to 62-mile Cardinal Greenway, longest trail in Indiana. Might see an eagle hunting along the river too. You will love it!

Feb 6 – 13

G$15,715 GYD per night

Guest favorite

Home in New Castle

4.99 out of 5 average rating, 132 reviews

Entire Home with Modern Conveniences - New Castle

This home has been equipped with everything you need for a relaxing stay. Unwind in the evening while watching your 65” TV. The updated kitchen offers plenty of space for cooking dinner.The first bedroom features a King size bed and room darkening window treatments. The second bedroom offers a designated office space w/ high speed internet and a trundle bed. To start your day well, the bonus room offers a coffee bar with Nespresso and wellness area complete with treadmill and yoga space.

Dec 10 – 17

G$24,519 GYD per night

Guest favorite

Guesthouse in Versailles

4.97 out of 5 average rating, 176 reviews

French B&B - Lower Level Apt w/ 2 bedrooms

The French Bed & Breakfast is nestled in the charming town of Frenchtown, Ohio. This B&B has been operating since 1999 and has accommodated many guests coming to visit Darke County. Lower level of our house - it has spacious and quaint accommodations for a reasonable rate. Included: Continental Breakfast, kitchen, great room & patio. Guest rooms on lower level: 2 bedrooms - can be rented individually or as a 2 bdrm apartment (pricing varies based on events - min $75 ea bdrm).

Sep 23 – 30

G$23,838 GYD per night

Guest favorite

Cottage in Richmond

4.95 out of 5 average rating, 378 reviews

The Cottage on Abington Pike - Earlham College

Charming private cottage (home) on the West edge of Richmond within walking distance to Earlham College. This updated Three bedroom home has one custom full bath (w/Tub) & one half bath. The kitchen has been updated and is on the lower level. Great location. Wooded private rear yard with covered patio. Cardinal Greenway, Gorge Trail all of Richmond nearby. Fast Wi-Fi. Large Living room & Game room w/Pinball & Multi-cade. Outside quiet 10:00PM. Parties not allowed. 2 Tvs.

Jun 24 – Jul 1

G$25,312 GYD per night

Superhost

Loft in Richmond

4.87 out of 5 average rating, 371 reviews

THE STARR LOFT- Earlham, IUEast, Historic District

Second floor of an 1865 Tin shop, industrial building. High, open beam ceilings & exposed brick walls. Bathroom features a soaker tub plus a lux walk in shower. The kitchen features quartz counters, a large farmhouse sink, really nice appliances and thoughtful touches everywhere. The wifi is excellent. Have issues with stairs? This is not a good choice for you. If you're up for stairs and want a unique slice of history in a hip package then you will not be disappointed.

Jun 29 – Jul 6

G$21,111 GYD per night

Guest favorite

Guesthouse in Muncie

4.86 out of 5 average rating, 303 reviews

Carriage House Loft Apartment

Welcome to our recently remodeled 1940 Carriage House Loft Apartment! We're happy to share our simple, comfortable, cozy space with you. Refurbished original hard wood floors with updated kitchenette area and bathroom. Charming and convenient, walk three blocks to the Cardinal Greenway & White River trails one mile to downtown Muncie! Perfect for 2 - 4 people, or a family with an infant/toddler. Enjoy self-check-in, privacy, & dedicated parking steps from the entrance.

Aug 7 – 14

G$14,706 GYD per night

Guest favorite

Home in Greenville

4.89 out of 5 average rating, 131 reviews

Explore Lake, Family-Trolling dock, Dogs, Spacious

Nestled within the serene surroundings of a picturesque lake community, this delightful Lake/Family home offers a charming blend of comfort and convenience. Boasting 2bd,2bt , A Spacious living room, large kitchen, paddle boat,dock and 17 lakes to enjoy. Located 1st house of 3 on a quiet dead end for nights of peaceful evenings on a large secluded deck. Beautiful area to take walks/ ride on bikes. Fire camp for cooking. We welcome up to 2 dogs, charge 99.00 for both.

Nov 16 – 23

G$31,946 GYD per night

Guest favorite

Guesthouse in Muncie

4.99 out of 5 average rating, 146 reviews

Burlingwood Guest House

You will feel a welcome peace when you enter the private wooded 6 acre property off of Burlington Drive. In a peaceful country setting just south of Muncie you'll enjoy our cozy and comfortable Guest House on this historic property. The setting includes a spacious patio, perfect for enjoying a cup of coffee surrounded by nature. Burlingwood is less than 10 minutes from Prairie Creek Reservoir, the Red Tail Nature Preserve, biking trails, and downtown Muncie.

May 15 – 22

G$17,443 GYD per night

Guest favorite

Home in Muncie

4.99 out of 5 average rating, 134 reviews

The BALL House

Completely remodeled 2 bedroom home near Ball State University. Walk to events, classes & activities. Comfortable furnishings, plenty of natural light. Living room, kitchen is fully equipped with all the necessary appliances and cookware for preparing meals at home. Comfortable bedrooms, backyard with patio. Easy access to public transportation & local shops/restaurants. Perfect for families or friends visiting the University. Have a Ball in the BALL house.

May 23 – 30

G$19,739 GYD per night

Guest favorite

Apartment in Fairmount

4.96 out of 5 average rating, 155 reviews

Enjoy Nostalgia In James Dean's Hometown

The Rebel Lodge is a fully restored historic brick building located in the heart of James Dean's hometown. Only a short walk to The Fairmount Historical Museum, and right around the corner from Main street. The building will sleep 4-5 with a comfy double bed, a pull out sofa and an additional sofa. It is decorated with fun mid century furniture and decor. Everything is freshly up to date with new furnace, & air conditioning. Please enjoy your stay!

Jun 26 – Jul 3

G$20,317 GYD per night

Guest favorite

Apartment in Greenville

4.98 out of 5 average rating, 125 reviews

Cozy one bedroom apartment in a Century old house

This first floor one bedroom apartment is in a quiet neighborhood just 4 blocks from Wayne Hospital, 5 blocks from Darke County Fairgrounds and a short 5 minute walk to Downtown Greenville. It sleep up 4. The living room has a queen size sofa bed. IT has a TV with Spectrum streaming app. WiFi is available. It has a fully equipped kitchen with coffee maker and microwave. Other features include a washer and dryer and free street parking.

Dec 23 – 30

G$16,167 GYD per night